Too Many Regrets
by Tyranusfan
Summary: Sam regrets many things in his life, but can he leave his guilt behind with Dean's help? My first Wing!fic. Set in the future. Extremely in the future. Rated K, it's pretty tame.


_This is my first Wing!fic, so be kind. Thanks to geminigrl11 for beta-ing, as always. This is an EXTREME future!fic. _

_I own nothing. Reviews craved._

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**Too Many Regrets**

Every year, Sam made three pilgrimages, one to Palo Alto, one to Skylawn Memorial in Hunter's Point, and one to Lawrence. It was a familiar journey, one he'd made so many times that he didn't even think about the routes. It was a private time for him. No hunting. Sometimes Sam saw things in his travels, dark creatures and their victims, but he passed them by. It was someone else's job on this day.

Letting go wasn't something a Winchester did well. It was a family trait, though no one could tell which side of the family it stemmed from. Sam figured it was his Dad. Dean still hadn't weighed in. Dad--- Well, Dad was Dad. Sam and John had made their peace, but, in the end they were just different, and that would never change.

Sam's attention drifted back to Jess' headstone. He was long out of tears, now he just felt cold when he looked at her grave. The marker was beautiful---so much more civilized than most of the ones he'd seen and dug up during his life---her parents had picked out a nice one. To him, though, it was inadequate. Jess had deserved so much more.

He moved on. Madison's grave was less ornate than Jessica's, a little more traditional. Sam had only seen her parents from a distance the day she was buried. He had been too raw with his own grief to explain to them---lie to them---about how he'd known their daughter. Besides, it had been such a brief relationship…no matter how deeply it had affected him. She'd been the first person Sam had truly opened up to after Jess. Well, besides his brother, but that was different, Maddy was the first woman. He'd let himself think there could be love with Madison. What a tragic mistake that had been. Too many hormones involved, not enough brains.

With Maddy, these trips always led to a profound sense of failure. It wasn't the same depth of grief he'd always felt with Jess, or his late wife, just a reminder of his youthful hubris and obsessive tendencies.

His last stop was Kansas, and Mom. It was raining by the time he got there. There was nothing in the ground here, unlike the other two. The yellow-eyed demon had made sure of that. Sam sometimes wondered why there had been nothing left of Mary, but there was of Jess. He'd never found an answer.

"I'm sorry," he whispered, staring glumly at the grave marker. He wanted to reach out and touch it, but he couldn't. It wasn't fair. They would all have had happy lives but for him and the demon's interest in him. Sam silently shook his head.

"I knew I'd find you here."

Sam jumped, startled, and turned to see Dean behind him, stealthy as ever. "Hey."

His brother said nothing, just stepped forward and joined Sam's vigil. "She never blamed you, Sam. You know that. None of them do."

Sam turned back to the grave, emotion that he thought long since abandoned swelling inside him, choking his voice. "I know…."

He heard the rustle behind him, but said nothing else as the strong wing surrounded him, blocking the rain and the chill. Dean's arm followed a moment later. His brother engaging in a rare show of emotion himself.

"Why do you do this to yourself, Sammy?" Dean whispered in his ear. "It's been two centuries, let it go."

"I owe them this much. I just don't want to forget, Dean."

"You should. They have. All they care about now is you."

Sam said nothing. He'd had this argument with his brother before; Dean simply wasn't going to change his mind.

Dean squeezed his shoulder. "I'm sorry I missed your birthday. Duty called and--- Well, that's no excuse, I guess. They said you'd gone out."

He didn't have to say who. Dad, Mom, Jess, Sarah, even Madison would still be there when they got back. Birthdays had never meant much to him the way they grew up, just a stepping stone to being more like his brother, and truly meant _nothing_ to them anymore, but still the others insisted he celebrate it. It was what family did.

"Just needed some air," Sam said wryly, but the smile didn't reach his eyes. Air was something else that meant little anymore.

"You go out for 'air' every time your birthday goes by. Worries the heck out of Sarah and Jess."

"They tell you where to find me?" Sam asked, more curious than upset. Sarah and Jess meant well, but they had never understood the weight of his guilt, and how seeing his family all together and happy every year just drove it home.

Dean smirked. "No one's ever had to tell me where to find my little brother. I just follow the dark cloud."

"I don't like it when you hunt alone. You should have waited for me." It was an irrational fear. Not much could hurt either of them nowadays.

"Well," Dean said casually, pulling Sam a little closer to keep him out of the shifting wind. "If I'd known it was gonna take so long, I would have waited. You needed the rest after that last one. Besides, you know how convincing He can be."

Sam fell silent, staring at the headstone again. They'd all lost so much because of him, because of his "gifts." Two hundred and seven years didn't dull the pain, even though he was with his family now almost every day. They were at last happy, why wasn't he?

"Come home, Sam."

"I missed you, yesterday," Sam murmured quietly.

"I know. Hey, tell you what, I'll let you use my sword the next time we go on a hunt. You know you want to."

Sam glanced at him, unable to prevent the smile from breaking out. Dean always could make him feel better. "That's thing is ridiculous. I think you're overcompensating for something."

Dean stepped back with a grin, dropping his wing away and tugging on Sam's arm. "Come on, before some yahoo with a salt gun sees you out here."

Finally, Sam relented and followed, raising a hand to his face. He heard a giant flap as he wiped his eyes dry, then unfurled his own wings and left the ground again. Maybe Dean was right. Maybe it was time for him to move on.

"Race you back," Dean challenged, his eyes sparkling.

"I always win, jerk," Sam called back, a smile forcing its way onto his face.

"In your dreams, Bird Boy."

END


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